21-O-Acetyl Dexamethasone 9,11-Epoxide

Base Information

• Chemical Name: 21-O-Acetyl Dexamethasone 9,11-Epoxide
• CAS No.: 2884-51-7
• Molecular Formula: C24H30O6
• Molecular Weight: 414.499
• European Community (EC) Number: 608-267-0
• UNII: SS5E88DK7N
• DSSTox Substance ID: DTXSID50452378
• Nikkaji Number: J2.715.481F
• Wikidata: Q82272974
• Mol file: 2884-51-7.mol

Synonyms:21-O-Acetyl Dexamethasone 9,11-Epoxide;2884-51-7;SS5E88DK7N;UNII-SS5E88DK7N;Dexamethasone acetate impurity F [EP];[2-[(1S,2S,10S,11S,13R,14R,15S,17S)-14-hydroxy-2,13,15-trimethyl-5-oxo-18-oxapentacyclo[8.8.0.01,17.02,7.011,15]octadeca-3,6-dien-14-yl]-2-oxoethyl] acetate;(9beta,11beta,16alpha)-21-(Acetyloxy)-9,11-epoxy-17-hydroxy-16-methylpregna-1,4-diene-3,20-dione;Pregna-1,4-diene-3,20-dione, 21-(acetyloxy)-9,11-epoxy-17-hydroxy-16-methyl-, (9beta,11beta,16alpha)-;SCHEMBL5707991;DTXSID50452378;MONKXVNQUJNHLQ-WMHQAVGRSA-N;DEXAMETHASONE ACETATE IMPURITY F [EP IMPURITY];9,11beta-Epoxy-17-hydroxy-16alpha-methyl-3,20-dioxo-9beta-pregna-1,4-dien-21-yl Acetate;(9.BETA.,11.BETA.,16.ALPHA.)-21-(ACETYLOXY)-9,11-EPOXY-17-HYDROXY-16-METHYLPREGNA-1,4-DIENE-3,20-DIONE;Acetic acid 3,20-dioxo-9beta,11beta-epoxy-16alpha-methyl-17-hydroxypregna-1,4-diene-21-yl ester;PREGNA-1,4-DIENE-3,20-DIONE, 21-(ACETYLOXY)-9,11-EPOXY-17-HYDROXY-16-METHYL-, (9.BETA.,11.BETA.,16.ALPHA.)-

Chemical Property of 21-O-Acetyl Dexamethasone 9,11-Epoxide

Chemical Property:

• Melting Point: 198-200 °C
• Boiling Point: 575.1±50.0 °C(Predicted)
• PKA: 12.51±0.70(Predicted)
• PSA: 93.20000
• Density: 1.29±0.1 g/cm3(Predicted)
• LogP: 2.53490
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Dioxane (Slightly), Methanol (Slightly)
• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 414.20423867
• Heavy Atom Count: 30
• Complexity: 919

Purity/Quality:

99.9% ^*data from raw suppliers

21-O-Acetyl dexamethasone 9,11-epoxide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CC2C3CCC4=CC(=O)C=CC4(C35C(O5)CC2(C1(C(=O)COC(=O)C)O)C)C
• Isomeric SMILES: C[C@@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@@]4([C@]35[C@@H](O5)C[C@@]2([C@]1(C(=O)COC(=O)C)O)C)C
• Uses: Dexamethasone intermediate.

Technology Process of 21-O-Acetyl Dexamethasone 9,11-Epoxide

There total 8 articles about 21-O-Acetyl Dexamethasone 9,11-Epoxide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

17α,21-dihydroxy-16α-methyl-1,4,9(11)-pregnatriene-3,20-dione 21-acetate (10106-41-9) → 21-acetoxy-9,11β-epoxy-17-hydroxy-16α-methyl-9β-pregna-1,4-diene-3,20-dione (912-38-9,2884-51-7,14622-51-6,98573-86-5)

Guidance literature:

With dichloromethane; tert-butyl alcohol; N-bromoacetamide; Reagens 4: wss. Perchlorsaeure, Erwaermen des Reaktionsprodukts mit Kaliumacetat in Aceton;

DOI:10.1021/ja01549a090

Reference yield:

17,21-dihydroxy-16α-methyl-pregna-1,4-diene-3,20-dione (19784-87-3) → 21-acetoxy-9,11β-epoxy-17-hydroxy-16α-methyl-9β-pregna-1,4-diene-3,20-dione (912-38-9,2884-51-7,14622-51-6,98573-86-5)

Guidance literature:

Multi-step reaction with 5 steps

1: mit Hilfe von Pestalotia foedans

4: sodium acetate; acetic acid

5: N-bromo-acetamide; dichloromethane; tert-butyl alcohol / Reagens 4: wss. Perchlorsaeure, Erwaermen des Reaktionsprodukts mit Kaliumacetat in Aceton

With dichloromethane; sodium acetate; acetic acid; tert-butyl alcohol; N-bromoacetamide;

DOI:10.1021/ja01549a090

Reference yield:

21-acetoxy-17-hydroxy-16α-methyl-11α-(toluene-4-sulfonyloxy)-pregna-1,4-diene-3,20-dione (115606-30-9) → 21-acetoxy-9,11β-epoxy-17-hydroxy-16α-methyl-9β-pregna-1,4-diene-3,20-dione (912-38-9,2884-51-7,14622-51-6,98573-86-5)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium acetate; acetic acid

2: N-bromo-acetamide; dichloromethane; tert-butyl alcohol / Reagens 4: wss. Perchlorsaeure, Erwaermen des Reaktionsprodukts mit Kaliumacetat in Aceton

With dichloromethane; sodium acetate; acetic acid; tert-butyl alcohol; N-bromoacetamide;

DOI:10.1021/ja01549a090

upstream raw materials:

17α,21-dihydroxy-16β-methyl-1,4,9(11)-pregnatriene-3,20-dione 21-acetate

17α,21-dihydroxy-16α-methyl-1,4,9(11)-pregnatriene-3,20-dione 21-acetate

17,21-dihydroxy-16α-methyl-pregna-1,4-diene-3,20-dione

21-acetoxy-17-hydroxy-16α-methyl-11α-(toluene-4-sulfonyloxy)-pregna-1,4-diene-3,20-dione

Downstream raw materials:

betamethasone 21-acetate

betamethasone

Acetic acid 2-((8S,9R,10S,11S,13S,14S,16R,17R)-9-chloro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxo-ethyl ester

C₂₉H₃₂O₈